Sodium borohydride → HCID 52914256, compound

Participants

Reaction Steps

2-(6,9-Difluoro-3-oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)benzaldehyde [(Example 39) 15 mg, 0.31 mmol] was dissolved in methanol (3 mL), treated with sodium borohydride (4 mg, 0.62 mmol, 2 equiv) and stirred at ambient temperature for 2 hours. The mixture was concentrated in vacuo and the residue was purified by silica gel gradient chromatography (100:0 to 80:20; dichloromethane:methanol), providing the titled compound: 1H-NMR (400 MHz, CDCl3) δ 8.46 (1H, s), 7.91 (1H, d, J=2.5 Hz), 7.75-7.70 (3H, m), 7.56 (1H, dd, J=7.3, 1.3 Hz), 7.45 (1H, td, J=7.6, 1.5 Hz), 7.38 (1H, td, J=7.4, 1.4 Hz), 7.30-7.17 (5H, m), 6.48 (1H, dd, J=2.4, 1.7 Hz), 5.66 (1H, d, J=2.4 Hz), 4.52 (2H, br s) ppm; high resolution mass spectrometry (ES+) m/z 484.1567 [(M+H)+; calculated for C27H20F2N5O2: 484.1580].

Provenance & Evidence